Recent research investigating the relationship between the global personality traits and job performance has offered evidence of criterion related validity. Specifically, Barrick and Mount (1991) identified conscientiousness while Tett, Jackson, and Rothstein (1991) identified agreeableness as most predictive of job performance across a variety of occupations and organizations. Using a contextual approach to trait measurement, results of the present study found both conscientiousness and agreeableness to be significantly related to retail assistant manager's and manager's job performance. These results were based on data collected from three retail organizations which included 110 assistant managers and 125 managers. Using the Big Five model as a guide, an inventory of five contextual trait scales with associated contextual trait statements was developed in accordance with the work environment of retail assistant managers and managers. A sample of 60 managers and 55 assistant managers was randomly selected for the purpose of contextual scale development and refinement. Using this sample, each contextual trait scale was refined using reliability and principle components analyses. The remaining 55 assistant managers and 65 managers were used for hypothesis testing to assess contextual trait differences and predictive validity. Results indicated no differences between assistant manager and manager groups on any of the five contextual trait measures. In terms of predictive validity, a hierarchical moderated regression model was constructed to assess the relationship between the five contextual traits, manager group, and interactions. The overall R2 was.31 with no significant changes due to manager group or interactions. Contextual trait scales measuring extroversion, agreeableness, conscientiousness, and openness to experience were significantly related to managerial job performance. However, contextual trait scale measuring extroversion revealed a negative beta weight. Implications of this finding are discussed with respect to suppressor effects and practical importance. Post hoc analysis using retail organization as a control variable indicated that only contextual trait scales measuring conscientiousness and agreeableness were significant predictors of retail assistant manager and manager job performance with an R$\sp2$ of.39. That is, 13 of the variance in managerial performance was due to organizations and 26 can be attributed to contextual traits..